In the mid-2000's, we saw Tulsa's emerging real estate market and had the opportunity to expand into the market where we have formed our division, TMC Property Management. 

Overnights are very very transient and come with unique challenges, think about these like a Motel 6, people arriving at all hours, tired, just need a place to crash as they make their way to their final destination.

This was not unique to a specific lender but some made the process easier then others for sure.Anyway, I am now approaching 75% LTV (based on initial purchase price) for the last investment property with PMI so I reached out to start the process and was denied with no explanation.

To me the perfect short term rental property needed to be unique.

For commercial asset classes, local credit unions can often be an excellent resource for more complicated or unique property types. 

I don't know anything about your property but I can tell you folks these days love a unique experience, so think about what you can offer to your guests and build the sites to cater to that experience.

And these are unique situations.. 

This is a very crowded space now, and what you've described is not particularly unique. 

Exclusive Use Clauses This is another challenging piece that is fairly unique to retail.

I wouldn't worry about squatters, it definitely happens, but I don't think Cleveland is uniquely worse than other larger cities, and there's a lot of steps you can take to help prevent this problem if you have a vacant property or something that's getting worked on or you're waiting to rent out.